Skip to Content
Merck

420120

Sigma-Aldrich

Juglone

A highly selective cell-permeable, irreversible inhibitor of PPlases (peptidyl-prolyl cis/trans isomerases of the parvulin family).

Synonym(s):

Juglone, 5-Hydroxy-1,4-naphthlenedione, 5-Hydroxy- p-naphthoquinone

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C10H6O3
CAS Number:
Molecular Weight:
174.15
MDL number:
UNSPSC Code:
51111800
NACRES:
NA.77

Pricing and availability is not currently available.

Quality Level

Assay

≥95% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

orange

solubility

DMSO: 10 mg/mL
ethanol: 10 mg/mL

shipped in

ambient

storage temp.

2-8°C

InChI

1S/C10H6O3/c11-7-4-5-9(13)10-6(7)2-1-3-8(10)12/h1-5,12H

General description

A highly selective cell-permeable, irreversible inhibitor of PPlases (peptidyl-prolyl cis/trans isomerases of the parvulin family). Other known PPlase inhibitors such as cyclosporin A, FK506, and rapamycin are not reported to inhibit the parvulin family of PPlases. The inactivation is shown to occur via the addition of thiol groups to juglone and not by any redox process. Exhibits bacteriostatic and fungistatic effects. Reported to be cytotoxic towards eukaryotic cells and to block transcription by RNA polymerase II.
Originally isolated from the fruit shells and leaves of walnut trees, juglone is a highly selective, cell permeable, irreversible inhibitor of the parvulin family of peptidyl-prolyl cis/trans isomerases (PPIase). Functions by covalently modifying sulfhydryl groups in the target enzymes. Exhibits bacteriostatic and fungistatic properties as well as cytotoxicity in eukaryotic cells. Also reported to directly block transcription in eukaryotic cells by RNA polymerase I, II, and III as determined by nuclear run-off (IC50 = 7 µM, 7 µM, and 2 µM, respectively). Disrupts formation of functional pre-initiation complexes via modification of sulhydryl groups, but does not significantly affect initiation or elongation. Does not inhibit restriction endonucleases or T7 RNA polymerase.

Biochem/physiol Actions

Cell permeable: yes
Primary Target
PPlases (peptidyl-prolyl cis/trans isomerases of the parvulin family)
Product does not compete with ATP.
Reversible: no

Packaging

Packaged under inert gas

Warning

Toxicity: Toxic (F)

Reconstitution

Following reconstitution aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

Other Notes

Chao, S.H., et al. 2001. Nucleic Acids Res.29, 767.
Hennig, L., et al. 1998. Biochemistry37, 5953.
Due to the nature of the Hazardous Materials in this shipment, additional shipping charges may be applied to your order. Certain sizes may be exempt from the additional hazardous materials shipping charges. Please contact your local sales office for more information regarding these charges.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Need A Sample COA?

This is a sample Certificate of Analysis (COA) and may not represent a recently manufactured lot of this specific product.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Nisreen Mohammed Al-Namnam et al.
Gene therapy, 28(10-11), 620-633 (2021-02-24)
Apert syndrome is a genetic disorder characterised by craniosynostosis and structural discrepancy of the craniofacial region as well as the hands and feet. This condition is closely linked with fibroblast growth factor receptor-2 (FGFR2) gene mutations. Gene therapies are progressively
Caixia Wu et al.
American journal of translational research, 13(10), 11162-11177 (2021-11-18)
Peptidyl-prolyl isomerase Pin1 is crucial for cell proliferation, but its role in pulmonary artery remodeling (PAR) is unclear. In the present study, we aimed to evaluate the expression and contribution of Pin1 in PAR. Treatment with Pin1 inhibitor Juglone or
Jia-Hua Hu et al.
Nature communications, 11(1), 1567-1567 (2020-03-29)
Voltage-gated K+ channels function in macromolecular complexes with accessory subunits to regulate brain function. Here, we describe a peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 (Pin1)-dependent mechanism that regulates the association of the A-type K+ channel subunit Kv4.2 with its auxiliary subunit

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service